This paper conceptualizes different grounds for collaborative decisions in order to forecast how different behaviors behave in a game-theoretical prisoner's dilemma (PD). Forecasting is facilitated by a simulated scenario between two actors. The paper views consequences of different behavioral strategies and underpins an evaluation through analyses of the game, and also presents a unique aggregated analysis modeling strategic behavior on the basis of game-theory. The paper suggests that game-theory could be a potential and powerful tool for researchers and practitioners struggling with the strategic dilemmas, i.e. trust-building versus opportunistic behavior in inter-firm cooperation. The paper outlines some strategic principles that may unsettle the dilemma situation through either social or formal contracts.